Journal
TETRAHEDRON LETTERS
Volume 48, Issue 20, Pages 3543-3547Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2007.03.108
Keywords
alpha-helix mimetics; benzamide scaffold; glucagon antagonists; inhibitors for protein-protein interaction
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A new alpha-helix mimetic was designed by using a benzamide as a rigid scaffold. It presents three functional groups corresponding to side chains of amino acids found at the i, i + 4, and i + 7 positions of an ideal alpha-helix, which are displayed on the same helical face. Its efficient synthesis was achieved by employing simple alkylation and amidation reactions which can be easily adapted for solid-phase synthesis. As a result, two tris-benzamides were produced to mimic two helical regions found in a peptide hormone, glucagon. (C) 2007 Elsevier Ltd. All rights reserved.
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